Methylamine → 2-(Methylamino)pyridine-4-carbonitrile

HRID 887636Notes

Reaction equation

HRID 887636 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][N:9]=1)[C:5]#[N:6].[CH3:10][NH2:11].C([O-])(O)=O.[Na+]>N1C=CC=CC=1.C1COCC1>[CH3:10][NH:11][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][N:9]=1)[C:5]#[N:6]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 516892Sodium BicarbonateHCID 5686382-Chloro-4-cyanopyridine

Product 1

HCID 219614802-(Methylamino)pyridine-4-carbonitrile

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-chloroisonicotinonitrile (22.0 g, 159 mmole) in pyridine (500 mL) was added methylamine in THF (2N, 160 mL), and NaHCO3 (54 g). The mixture was heated to 120° C. in a sealed vessel for 40 h. After cooled to RT, the mixture was filtered and the filter cake was washed with CH2Cl2. The combined filtrated was concentrated in vacuo to give a yellow solid (21 g) as the desired compound.

Workup

  1. temperatureAfter cooled to RT
  2. filtrationthe mixture was filtered
  3. washthe filter cake was washed with CH2Cl2
  4. filtrationThe combined filtrated
  5. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-dc279dcae4604efeabf4d69733ae5730
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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